10 days in Puerto Rico Itinerary

10 days in Puerto Rico Itinerary

Created using Inspirock Puerto Rico trip itinerary builder

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Route & dates

10 days in Puerto Rico Itinerary

Start: Chicago
Fly:  9​h 30​min
1
Isla de Vieques
— 3 nights
Drive + Fly:  2​h 15​min
2
Culebra
— 3 nights
Fly:  30​min
3
San Juan
— 2 nights
Fly:  7​h 45​min
End: Chicago

3
nights
Isla de Vieques

Isla de Vieques ©
For sixty years until 2003, most of the Isla de Vieques was closed off to the public, with the US Navy using the island's beaches and surrounding waters for drills and testing of new military machinery, such as bombs.
Explore hidden gems such as Stand-Up Paddleboarding and La Chiva. You'll enjoy a bit of beach vacationing at Sun Bay and Media Luna Beach. Next up on the itinerary: enjoy the sand and surf at Caracas Beach, take in the waterfront at Malecon, shop like a local with Siddhia Hutchinson Fine Art Gallery, and tour the pleasant surroundings at Navio Beach.

To see other places to visit, photos, ratings, and more tourist information, read our Isla de Vieques tour planning app .

Chicago, USA to Isla de Vieques is an approximately 9.5-hour flight. You can also do a combination of flight, shuttle, and ferry. The time zone difference moving from Central Standard Time (CST) to Atlantic Standard Time (AST) is 2 hours. While traveling from Chicago, expect a bit warmer days and warmer nights in Isla de Vieques, ranging from highs of 85°F to lows of 76°F. Finish up your sightseeing early on the 11th (Sat) so you can travel to Culebra.

Things to do in Isla de Vieques

Outdoors Beaches Parks
Highlights from your plan
La Chiva ©
La Chiva
Caracas Beach ©
Caracas Beach
Stand-Up Paddleboarding

3
nights
Culebra

Culebra ©
With much of Culebra a nature refuge, the tropical island has been protected from overdevelopment, chain hotels, and the cruise set.
You'll enjoy a bit of beach vacationing at Zoni Beach and Carlos Rosario Beach. Explore hidden gems such as Tamarindo Beach and Playa Punta Soldado Beach. Next up on the itinerary: stroll through Flamenco Beach, step off the mainland to explore Culebrita Island, visit a coastal fixture at Culebrita Lighthouse, and get lost in a book at Culebra Public Library.

To see other places to visit, reviews, where to stay, and other tourist information, you can read our Culebra sightseeing planning website .

You can do a combination of car and flight from Isla de Vieques to Culebra in 2.5 hours. Another option is to ride a ferry. In May, daily temperatures in Culebra can reach 87°F, while at night they dip to 77°F. Cap off your sightseeing on the 14th (Tue) early enough to catch the flight to San Juan.

Things to do in Culebra

Parks Outdoors Beaches
Highlights from your plan
Flamenco Beach ©
Flamenco Beach
Tamarindo Beach ©
Tamarindo Beach
Carlos Rosario Beach ©
Carlos Rosario Beach

2
nights
San Juan

San Juan ©
Founded by the Spanish in 1521, San Juan is the oldest city under U.S.
On the 15th (Wed), steep yourself in history at San Juan National Historic Site, explore the different monuments and memorials at San Juan Cemetery, and then take a memorable tour with Tours. On the 16th (Thu), you'll have a packed day of sightseeing: appreciate the extensive heritage of Paseo de la Princesa and then take a stroll through Old San Juan.

To see where to stay, traveler tips, other places to visit, and more tourist information, read our San Juan trip builder site .

San Juan is very close to Culebra. Expect a daytime high around 88°F in May, and nighttime lows around 76°F. Wrap up your sightseeing on the 16th (Thu) to allow time to travel back home.

Things to do in San Juan

Historic Sites Outdoors Tours
Highlights from your plan
Paseo de la Princesa ©
Paseo de la Princesa
Zipline

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